Cis-4,5-didehydro-11-deoxy-13,14-dihydro-PG compounds

ABSTRACT

This invention relates to a group of cis-4,5-didehydro-11-deoxy-PG 1  analogs having variable chain length, optional methyl substitution in the methyl-terminated side-chain, and processes for making them. These compounds are useful for a variety of pharmacological purposes, including ulcer treatment, inhibition of platelet aggregation, increase of nasal patency, and labor induction at term.

This application is a division of Ser. No. 548,586, filed Feb. 10, 1975, now issued as U.S. Pat. No. 3,987,072.

The present invention relates to prostaglandin analogs, for which the essential material constituting a disclosure thereof is incorporated by reference here from U.S. Pat. No. 3,987,072, issued Oct. 19, 1976. 

We claim:
 1. A compound of the formula ##STR1## or a mixture comprising that compound and the enantiomer thereof; WHEREIN W is ##STR2## wherein g is 2 to 4, inclusive; WHEREIN L₁ is ##STR3## or a mixture of ##STR4## wherein R₃ and R₄ are hydrogen or methyl, being the same or different,Wherein M₁ is ##STR5## wherein R₅ and R₆ are hydrogen or methyl, with the proviso that R₅ is methyl only when R₆ is hydrogen and R₆ is methyl only when R₅ is hydrogen; Wherein R₁ is hydrogen, alkyl of one to 12 carbon atoms, inclusive, cycloalkyl of 3 to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive, or a pharmacologically acceptable cation; and Wherein R₇ is --(CH₂)_(m) --CH₃, wherein m is one to 5, inclusive.
 2. A compound according to claim 1, wherein W is ##STR6##
 3. A compound according to claim 2, wherein W is ##STR7##
 4. A compound according to claim 2, wherein W is ##STR8##
 5. A compound according to claim 1, wherein W is ##STR9##
 6. A compound according to claim 5, wherein M₁ is ##STR10##
 7. A compound according to claim 5, wherein M₁ is ##STR11##
 8. A compound according to claim 7, wherein m is
 3. 9. A compound according to claim 8, wherein g is
 4. 10. A compound according to claim 9, wherein R₃ is hydrogen and R₄ is methyl.
 11. A compound according to claim 9, wherein R₃ and R₄ are methyl.
 12. A compound according to claim 11, wherein R₅ is methyl.
 13. A compound according to claim 11, wherein R₆ is methyl.
 14. A compound according to claim 11, wherein R₅ and R₆ are hydrogen.
 15. 2a,2b-Dihomo-cis-4,5-didehydro-11-deoxy-16,16-dimethyl-13,14-dihydro-PGE₁, a compound according to claim
 14. 16. A compound according to claim 9, wherein R₃ and R₄ are hydrogen.
 17. A compound according to claim 16, wherein R₅ and R₆ are hydrogen.
 18. A compound according to claim 16, wherein R₆ is methyl.
 19. A compound according to claim 16, wherein R₅ is methyl.
 20. 2a,2b-Dihomo-cis-4,5-didehydro-11-deoxy-15-methyl-13,14-dihydro-PGE₁, a compound according to claim
 19. 21. A compound according to claim 8, wherein g is
 2. 22. A compound according to claim 21, wherein R₃ is methyl and R₄ is hydrogen.
 23. A compound according to claim 22, wherein R₅ and R₆ are both hydrogen.
 24. Cis-4,5-Didehydro-11-deoxy-16-methyl-13,14-dihydro-PGE₁, a compound according to claim
 23. 25. A compound according to claim 19, wherein R₃ and R₄ are hydrogen.
 26. A compound according to claim 25, wherein R₅ and R₆ are hydrogen.
 27. Cis-4,5-Didehydro-11-deoxy-13,14-dihydro-PGE₁, a compound according to claim
 26. 28. A compound according to claim 25, wherein R₆ is methyl.
 29. Cis-4,5-Didehydro-11-deoxy-13,14-dihydro-PGE₁, 15-methyl ether, a compound according to claim
 28. 30. A compound according to claim 25, wherein R₅ is methyl.
 31. Cis-4,5-Didehydro-11-deoxy-15-methyl-13,14-dihydro-PGE₁, a compound according to claim
 30. 32. Cis-4,5-Didehydro-11-deoxy-15-methyl-13,14-dihydro-PGE₁, methyl ester, a compound according to claim
 30. 33. A compound according to claim 31, wherein R₃ and R₄ are methyl.
 34. A compound according to claim 33, wherein R₅ and R₆ are hydrogen.
 35. Cis-4,5-Didehydro-11-deoxy-16,16-dimethyl-13,14-dihydro-PGE₁, a compound according to claim
 34. 36. Cis-4,5-Didehydro-11-deoxy-16,16-dimethyl-13,14-dihydro-PGE₁, methyl ester, a compound according to claim
 35. 37. A compound according to claim 33, wherein R₅ is methyl.
 38. Cis-4,5-Didehydro-11-deoxy-15-methyl-16,16-dimethyl-13,14-dihydro-PGE₁, a compound according to claim
 27. 39. A compound according to claim 33, wherein R₆ is methyl.
 40. Cis-4,5-Didehydro-11-deoxy-16,16-dimethyl-13,14-dihydro-PGE₁, 15-methyl ether, a compound according to claim
 39. 